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America’s landscapes — its rural towns and big cities, its open plains and mighty rivers — have provided inspiration for some of our most beloved and acclaimed literary works. Check out this lit-themed road trip from Oregon to Maine, and visit the places where authors like Willa Cather, F. Scott Fitzgerald, and Mark Twain lived and worked.

Literary Road Trip — Portland, OR to Bangor, ME

Portland, Oregon

Start your pilgrimage at a legendary mecca for readers: Powell’s City of Books. Covering an entire city block and stocking no less than a million volumes, Powell’s is the world’s biggest independent bookstore. Pick up a few tales to read on your journey and then hit the road.

Ketchum, Idaho

Head east on I-84 through the Columbia River Valley and drive to Ketchum in the rugged mountains of central Idaho. Ernest Hemingway spent his final years here, on a secluded estate above the Big Wood River just north of downtown. The house isn’t open to the public, but you can visit Hemingway’s modest grave at the Ketchum Cemetery (1026 North Main Street).

Riverton, Wyoming

Continue east via US-20 and cross into Wyoming on US-26, keeping an eye out for bison as you pass the iconic pinnacles of Grand Teton National Park. Your next stop is Riverton, where much of Annie Proulx’s short story Brokeback Mountain was set. The mountain doesn’t actually exist, but you can visit the Riverton Post Office where Ennis sent his postcard to Jack.

Denver, Colorado

Next, head south via US-287 and I-80 to Denver. The narrator of Jack Kerouac’s classic On the Road passed through Denver many times. Make a stop at My Brother’s Bar (Fifteenth and Platte), where Kerouac and Neal Cassady, the model for Dean Moriarty in the novel, were regulars.

Red Cloud, Nebraska

Go east on I-70 and continue on US-36 through the rolling prairies of eastern Colorado and Nebraska. Stop in Red Cloud to visit the home where Willa Cather lived from 1885-1890. The Nebraska landscape had a profound effect on Cather and influenced many of her works.

Iowa City, Iowa

Cut north back to I-80 and head east to Iowa City, designated a UNESCO City of Literature in 2008 and home to the acclaimed Writer’s Workshop at the University of Iowa. Many important authors have been involved with the workshop. In fact, Kurt Vonnegut, Jr. spent 2 years teaching here, from 1965 to 1967.

Stroll down the Literary Walk on Iowa Avenue, which showcases the work of 49 writers who have connections to Iowa. Then, drive past the Vonnegut House at 800 North Van Buren Street, where the author began work on his classic novel Slaughterhouse-Five.

Oak Park, Illinois

Continue via I-80 and I-88 to Oak Park, the leafy, historic Chicago suburb where Ernest Hemingway was born. Take a tour of the Hemingway Birthplace and Museum to learn about his early years. You might plan your visit to coincide with Oak Park’s annual Hemingway Birthday Bash and Hemingway 8K Running of the Bulls footrace (no actual bulls involved). This year’s event is happening July 15-17.

Indianapolis, Indiana

Make your way to I-65 and head south toward Indianapolis, where Kurt Vonnegut was born (and a place he often used to represent middle-class American values). Stop in at the Kurt Vonnegut Memorial Library, which displays a collection of his doodles, letters, and personal artifacts. The library holds a Vonnegut Fest every November.

Mansfield, Ohio

Continue east along I-70 to Columbus, Ohio, then northeast on I-71. Make a stop at the Ohio State Reformatory in Mansfield. The Oscar-nominated movie The Shawshank Redemption, based on Stephen King’s short story, was filmed at this imposing prison.

New York City, New York

Link up with your old friend I-80 and follow it across Pennsylvania into New York. Your next stop is Manhattan. Head first to St. Patrick’s Cathedral (5th Avenue between 50th and 51st Streets) — F. Scott and Zelda Fitzgerald were married in the adjoining rectory in 1920. Just 9 blocks uptown is the famous Plaza Hotel. The Fitzgeralds spent many a madcap evening here, even reportedly frolicking in the Pulitzer fountain out in front. Scott set much of his second novel, The Beautiful and the Damned, at The Plaza, as well as a pivotal scene from The Great Gatsby (in which Tom confronts Gatsby about his feelings for Daisy). The Plaza is also where Truman Capote held his legendary Black and White Ball, the so-called “Party of the Century,” in 1966.

Near the Plaza on 38 West 59th Street is the apartment where the Fitzgeralds lived for their first year of marriage. Other notable New York addresses include 228 East 48th Street, where Vonnegut lived for over 40 years, and 206 East 72nd Street, where John Steinbeck wrote East of Eden.

Long Island, New York

Next, cross the Robert F. Kennedy Bridge and take I-278 and I-295 to Long Island, where the Fitzgeralds lived from 1922 to 1924. Drive past the Fitzgeralds’ former home at 6 Gateway Drive in Great Neck, the tony suburb that served as the model for West Egg in The Great Gatsby (he began writing the novel here). Then, take a tour of Oheka Castle in Huntington. This sprawling, opulent estate may have served as the inspiration for Gatsby’s lavish mansion.

Hartford, Connecticut

Head back to the mainland and take I-95 northeast to Hartford. Mark Twain, though most closely associated with Missouri and the Mississippi River, spent a large portion of his life in Hartford. Stop in at the Mark Twain House & Museum, where Twain lived from 1874 to 1891 and wrote many of his most celebrated works, including The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn.

Concord, Massachusetts

Continue northeast on I-84 towards Massachusetts. This richly historic state is a treasure trove of literary landmarks, from Melville’s Berkshire farmstead to Hawthorne’s House of the Seven Gables, but you’ll get the most bang for your buck in Concord. You can choose to visit Henry David Thoreau’s Walden Pond; the home where Ralph Waldo Emerson penned his greatest works; or Orchard House, where Louisa May Alcott lived and where her beloved novel Little Women was set.

Bangor, Maine

If you managed to read all the way through The Shining, driving a few more hours north won’t scare you. Your road trip ends in Bangor, where master of horror Stephen King currently lives. Fans debate whether Bangor or the small town of Dexter was the model for the fictional town of Derry, where King set a number of novels including It,Dreamcatcher, and Insomnia. (In 1983, though, King himself told the Bangor Historical Society that Derry was based on Bangor.)

Landmarks from the books include the Thomas Hill Standpipe (which, as the Derry Standpipe, is the scene of a terrifying encounter with Pennywise the Clown in It); the Paul Bunyan statue (which came horribly to life in It); and the Bangor Auditorium (aka the Derry Civic Center featured in Insomnia).

As you cross the country on this literary pilgrimage, your journey will no doubt generate some memorable tales of its own. Before you set out on this or any road adventure, be sure you have the right car insurance coverage.

Esurance and this website are not affiliated with, maintained, authorized, endorsed or sponsored by the authors listed in this post or any of their respective affiliates.

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about Ellen

Ellen has spent many years as a professional wordsmith, helping to shed light on such topics as world travel, cargo pants, and the porosity of bath tiles. As a freelance copywriter for Esurance, she brings her boundless curiosity to the world of insurance. Outside work, she can be found cheering on the San Francisco Giants, hiking in the Oakland hills, and (barely) resisting smuggling penguins home from Antarctica.